SU547169A4 - Composition for controlling phytopathogenic fungi - Google Patents

Description

Table 1

N-d, H AQ J-w

NKCNRC -X n.) 0

Table 3

NHCNHiiOOCH,.

I

Compound

table 2

K N fc

NHtNHt-X J 0

4 - (2 - Methylene Aminophenyl) - 3 - Thiol alofanates of the invention are excellent fungicides.

These compounds were pre-assessed using a Compound concentration of 300 ml for spraying the seedlings with liquid at a flow rate of about 150 gallons per acre (about 1500 l / ha). The solution or suspension was prepared by dissolving a weighed amount of the test fugicicide in a mixture of acetone and methanol (50:50), followed by the addition of an equal volume of water.

JH NH

L

 S

NW

-ABOUT

The general method of fungicidal testing was as follows.

Plants in pots were placed under growth conditions conducive to the development of the diseases to be assessed, then the plants were sprayed on a moving belt and dried. Then, the respective plants were inoculated with the desired spores of the fungus and incubated before the onset of disease symptoms and their development; then the extent of disease reduction was noted or assessed according to the following scale:

Disease Reduction Percentage

97-100

90-96

70-89

50-70

50, inactive

The plants and their diseases are given in table. 4. The degree of disease reduction according to preliminary estimates is given in Table. five.

Then repeated and special tests were carried out and, as described below.

A. Study of the effects of various doses.

1. Fighting powdered mildew on beans.

The seedlings of the beans were sprayed before being drained with various concentrations of liquids, using two samples in each experiment. The plants were allowed to dry for 20 hours, then they were inoculated with a spore suspension of Egesiphe polygoni containing 2 × 10 spores in 1 ml. Inoculated and control plants were kept in a greenhouse at 23.9-26.7 ° C in those high humidity.

Table 4

Table 5

dash 10 days. Then, the number of plants damaged by altitude was calculated, and the percentage reduction of the disease was calculated using the formula.

Disease Reduction -

The number of damaged on the control-the number of damaged on the treated

huo

Number of damaged on control

The results are given in Table. 6

Table 6

35

40

The degree of reduction of the disease at the concentration of the compound

Pry.chechenie 1 lb 453 g; 1 gallon 3.78 l.

2. Fighting powdered mildew on cucumbers.

Cucumber seedlings with two well-developed primary leaves and small third primary leaves were sprayed before being drained with various concentrations of methyl 4 - 2 - (furfurylidene o) -phenyl-3-thioallophanate solution (α-compound 1). The foliage of the plants was allowed to dry for several hours, then inoculated with a spore suspension of Sphaerotheca fuliginea containing about 2X10 ascospores in 1 ml. The plants were immediately placed in a greenhouse at 23.9-26.7 ° C; 11 days after treatment with chemicals, the disease is sufficient

evolved, made definitions; the percentage of disease reduction was calculated. Got the following results:

Percent reduction

concentration, disease. mi

100 50 25 12.5 100

99.6

6.3

97.9

3.1

94.3

72.5

1.6

B. Residual activity after weathering.

The weather resistance of the proposed fungicides was determined (compound 17). Sprinkling was carried out after applying the chemicals before inoculation with phytopathogenic fungal spores. In tab. 7 summarizes the results obtained for various plant diseases.

B. Systemic testing by root uptake.

1. Combating rice disease (Piricularia oryzae).

Sines of rice 1-3 inches tall (25-

75 mm) planted in plastic pots

45 with a diameter of 75 mm. Compound 17 dissolved

Table 7 pounds per 100 gallons

in a mixture of acetone, methanol and water (1: 1: 2) and the concentration was adjusted so that 15 ml of the solution containing the pre-name) could be dissolved

chenny dose

in water and irrigate the plants by watering the soil. The rice plants thus treated were kept in standard greenhouse conditions at about 26.7 ° C for 8 days. The plants were inoculated with P. oryzae spores and after 6 days, the percentage of disease reduction was calculated. Got the following results:

% reduced; 1 disease

91.7 98.0

2. Fighting powdered mildew on cucumbers (Sphaerotheca fuliginea).

Cucumber plants with two well-developed leaves in plastic pots with a diameter of 75 ml were irrigated with 15 ml of a solution containing various concentrations (million) of compound 17. Then the plants were inoculated by applying leaves of a S. fuliginea spore suspension containing 2 x 10 ascospores per 1 ml. Inoculated plants were immediately placed in a greenhouse at 29.4-32.2 ° C and were periodically monitored for the development of the disease. Got the following results:

Level of disease decline after 6 weeks

E

BUT

In order to determine the duration of the systemic activity of compound 17, cucumber plants used in the weather tests specified in clause B. were kept and periodically inspected. Got the following results:

Number of weeks

The minimum concentration to ensure a 50% after the destruction of a mildew, million chiquim on foliage without rain and rain

75

150

3 600 150

4 5 600 300

The compounds of the invention provide a good reduction in disease at low doses more than 5 weeks after application of the liquid to the foliage or to the soil.

3. Fighting powdered mildew on wheat (Erysiphe graminis).

Soil irrigation.

Plants aged 5-7 days in plastic pots were cut to a height of 37.51 mm, and the soil was sprinkled with 15 ml of an aqueous solution of compound 17 (type compound of the invention). The plants were then kept in a greenhouse at a temperature of about 23.9 ° C for two days, then inoculated with spores from wheat plants infected with a powdery mildew. The onset of the disease was noted 6 days after inoculation. Received the results given in table. eight.

Table 8

15

Seed processing Wheat seeds were treated with various doses of compound 17. To do this, 40 g of seeds were shaken in a dish with 1 ml of acetone and 0.5 ml of water with such an amount of compound in order to obtain concentrations

0.5; one; 2 or 4 ounces per 100 pounds (0.35; 0.7; 1.4 or 2.8 g / kg). The treated seeds were planted in the soil in pots with a diameter of 63 mm, applied in each: treatment with 4 experiments. The pots were kept in a greenhouse at 21.1 -

23.9 ° C until the seedlings reached a height of about 50 mm. Plants were inoculated by applying a spore suspension of E. graminis containing about 30,000 spores per ml. The plants were dried, pulled out in a greenhouse at

21.1-23.9 ° C to develop the disease. 17 days after planting, the disease was observed and the level of disease reduction was determined, the results are shown in Table. 9.

45

Table 9

The level of disease reduction at the dose of the compound, g / kg

Compound

50

G. Experiments to eradicate. Cucumber plants in the two-leaf stage were inoculated with a spore suspension of Sphaerotheca fuliginea containing about 2 X 10 ascospores per ml. After 48 hours, the plants were sprayed with a solution of the test compound of various concentrations. After 10 days, the extent of the disease was determined by counting the number of lesions, and also the percentage was calculated.

root of disease by comparison with the number of lesions on untreated plants. The results are shown in Table. ten.

Table 10

D. Fighting rot when storing fruit, such as peach brown rot (Monilia fructkola), with the help of a perch of fruit after harvest.

After harvesting, the partially washed peaches were immediately immersed in a solution of the test compound in a mixture of acetone, methanol, and water (1: 1: 2) with concentrations of 300 or 600 ppm. It was then dried at room temperature and inoculated with a spore suspension of Monilinia fructicola 30x10 spores in 1 ml. The fruit was then held at 24.4 and 14.5 ° C until brown rot appeared on the control samples. Received the results given in table. eleven.

Table 11 E. Comparison with known compounds. Compound 1 and known compounds from British Patent No. 1214415 were compared. 55 1. Fighting rice disease (Piricularia oryzae). Rice plants were sprayed with foliage with test compounds of different concentrations (ppm) and inoculated, as described above, with rice disease. A direct comparison was made with the following compounds from English patent no. 1214415: I - 1 - benzylideneamino - 2 - (3 - methoxycarbonyl - 2 - thioureid) - benzene; 65

12

II- 1 - (4 - chlorobenzylideneamino) -2- (3methoxycarbonyl - 2 - thioureid) - benzene;

III - 1 - (4 - methoxybenzylidene) -2 (3 - methoxycarbonyl - 2 - thioureid) -benzene;

IV- 1 - (3 - nitrobenzylndenamino-2- (3ethoxycarbonyl - 2 - thioureid) - benzene.

The results are shown in Table. 12.

Table 12

2. Experiments to determine the zone of inhibition for various fungal microorganisms.

20 ml of potato dextrozone agar (RDA) was placed on a plastic plate (9 € m). Solutions of different concentrations of the test fungicidal compound were prepared. An antibiotic disk (6.35 mm) was immersed in each solution, then it was placed in the center of the agar plate. On opposite sides on the edges of Petri plates, mats of the mycelium of several fungi were placed on the surface of the agar. The plates were then kept under conditions that promoted the growth of the respective microorganisms. After 3-6 days, growth was noted and the zones of inhibition and were determined. The following scale was used to determine the degree of inhibition: - | -I- | - strong, + + medium, + weak, - no inhibition. In tab. 13 summarizes the test results. G. Effect of fungicides on fermentation of grape juice. It is desirable that the fungicides used for the fence should not affect the rate of fermentation of the grape juice used in winemaking. Compound 17 was investigated in comparison with the well-known fungicide, Folpet - N-trichloromethylthiophthalimide. For this experiment, the fermentation medium consisting of 3785 ml of grape juice and 454 g of glucose was divided into 200 ml portions and placed in 0.5 l thick bags containing test compounds dissolved in acetone / mixture

13

14 Table 13